Startup founders who raised $15 million explain what everyone gets wrong about quitting your job to start a company

TheSkimm Carly Zakin Danielle Weisberg
‘Quitting our jobs, it was the scariest day of our life,’ said Carly Zakin and Danielle Weisberg, founders of theSkimm (pictured). Courtesy of theSkimm

Before founding theSkimm in the summer of 2012, Carly Zakin and Danielle Weisberg worked together at NBC.

As the roommates considered starting their company, which today provides short news updates to 5 million subscribers at 6 a.m. every morning, they enrolled in a Skillshare class about finding a business partner taught by investor and entrepreneur Alex Taub.

Speaking with Business Insider US editor in chief Alyson Shontell on an episode of Business Insider’s podcast “Success! How I Did It,” Zakin and Weisberg said that Taub became a mentor and was one of the first to give them career — and life — changing advice:

“If you’re going to start something, you need to be all in. How can you ask anyone to even think about giving you money if you have not made sacrifices to prioritise the effort yourself?'”

And they did it. But although quitting their jobs to start a company might seem like a romantic origin story, they told Shontell, people have it wrong — or at least, they’re missing some critical elements. Weisberg continued:

“Quitting our jobs, it was the scariest day of our life. That was not easy. And those first months … every point of this company has been hard. That’s the case anytime you’re building something. But those first months, we only got through it because we didn’t have a backup plan. We didn’t have a safety net financially or emotionally. This was everything.”

That was our saving grace, because there was no plan B. There was only, ‘We’re on our couch, we can’t afford cable, we’ve maxed out our credit cards, our parents are giving us hugs.’ But that was the support. Carly’s parents made us a lot of dinner. That was it. There was nowhere else to go.”

In fact, Zakin said, they never had the money to quit in the first place. “‘Bootstrap’ is such a generous term because it makes it seem like we had money to bootstrap,” she said. “We worked in media in mid-level jobs. We had just over $US4,000 between the two of us. We lived in a rent-stabilised apartment downtown and agreed to go into credit card debt together.” (They paid it off just recently.)

Plus, investors had no interest. Weisberg explained:

“So when everyone was saying no, and we made a list of all of the people — all of the investors, angels, seed funds — and we would turn anyone who said ‘no’ red. And then the whole list, which was a lot of names, was completely red. I remember a day in our kitchen, we had just gotten off a pitch that again ended with ‘Thanks so much, not interested,’ and we just had to make a decision. Are we going to go for this or are we going to go try to get jobs freelancing for the 2012 election?

“It wasn’t really even a decision — it was just a half-second to reevaluate where we were, change our pitch a bit, and that was it. That was the closest we’ve ever come to a crisis of confidence in this company. If you let those things get to you early on, then you don’t know what else is coming. There are going to be a lot more challenges.”

Now, having raised more than $US15 million of funding and with theSkimm well-established as successful startup, Zakin said she struggles with how to advise people who come to them asking for advice on starting a business, but who say they can’t afford to quit their day jobs.

“I still have mixed feelings about what to tell them,” she said. “Who am I to tell someone what financial decisions they should make? But for us, we were asking people to believe in us, and we had to show that we believed in us so much that we were willing to take a huge risk ourselves, quit our jobs, have no financial security, and give it a shot.”

Listen to the full podcast interview:


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